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Volume 69 
Part 3 
Page o421  
March 2013  

Received 9 December 2012
Accepted 14 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.006 Å
R = 0.051
wR = 0.191
Data-to-parameter ratio = 12.8
Details
Open access

(E)-N'-(4-Fluorobenzylidene)-2-(3-methylphenyl)acetohydrazide

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C16H15FN2O, the dihedral angles between the benzene rings are74.7(8), 74.1 (1), 74.2 (7) and 74.3 (5)° in the four independent molecules in the asymmetric unit. In the crystal, N-H-O hydrogen bonds involving the hydrazide and acetyl groups, which form R22(18) ring motifs, link the molecules into dimers, which form columns along [010].

Related literature

For Schiff bases as ligands for complexation of metal ions, see: Aydogan et al. (2001[Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.]); their applications as dyes and pigments, see: Taggi et al. (2002[Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.]) and crystallography and coordination chemistry, see: Kundu et al. (2005[Kundu, N., Chatterjee, P. B., Chaudhury, M. & Tiekink, E. R. T. (2005). Acta Cryst. E61, m1583-m1585.]); Xu et al. (1997[Xu, Z., Thompson, L. K. & Miller, D. O. (1997). Inorg. Chem. 36, 3985-3995.]). For related structures, see: Fun et al. (2011a[Fun, H.-K., Hemamalini, M., Sumangala, V., Prasad, D. J. & Poojary, B. (2011a). Acta Cryst. E67, o2847.],b[Fun, H.-K., Hemamalini, M., Sumangala, V., Nagaraja, G. K. & Poojary, B. (2011b). Acta Cryst. E67, o2835.], 2012[Fun, H.-K., Quah, C. K., Frank, P. V., Damodara, N. & Kalluraya, B. (2012). Acta Cryst. E68, o2192.]); He & Shi (2011[He, G.-F. & Shi, Z.-Q. (2011). Acta Cryst. E67, o48.]); Odabasoglu et al. (2007[Odabasoglu, M., Büyükgüngör, O., Sunil, K. & Narayana, B. (2007). Acta Cryst. E63, o4145-o4146.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15FN2O

  • Mr = 270.30

  • Triclinic, [P \overline 1]

  • a = 11.8535 (7) Å

  • b = 12.3769 (9) Å

  • c = 20.8721 (11) Å

  • [alpha] = 98.549 (5)°

  • [beta] = 103.074 (5)°

  • [gamma] = 105.134 (6)°

  • V = 2808.2 (3) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.74 mm-1

  • T = 173 K

  • 0.22 × 0.16 × 0.08 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.780, Tmax = 1.000

  • 16410 measured reflections

  • 9250 independent reflections

  • 3807 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.191

  • S = 0.99

  • 9250 reflections

  • 725 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1A...O1Bi 0.86 2.01 2.868 (3) 173
N1B-H1B...O1Ai 0.86 2.00 2.860 (3) 173
N1C-H1C...O1Dii 0.86 2.01 2.865 (3) 173
N1D-H1D...O1Ciii 0.86 2.00 2.857 (4) 173
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y-1, z-1; (iii) x+1, y+1, z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2277 ).


Acknowledgements

ASP thanks the UOM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Aydogan, F., Ocal, N., Turgut, Z. & Yolacan, C. (2001). Bull. Korean Chem. Soc. 22, 476-480.  [ChemPort]
Fun, H.-K., Hemamalini, M., Sumangala, V., Nagaraja, G. K. & Poojary, B. (2011b). Acta Cryst. E67, o2835.  [CSD] [CrossRef] [details]
Fun, H.-K., Hemamalini, M., Sumangala, V., Prasad, D. J. & Poojary, B. (2011a). Acta Cryst. E67, o2847.  [CSD] [CrossRef] [details]
Fun, H.-K., Quah, C. K., Frank, P. V., Damodara, N. & Kalluraya, B. (2012). Acta Cryst. E68, o2192.  [CSD] [CrossRef] [details]
He, G.-F. & Shi, Z.-Q. (2011). Acta Cryst. E67, o48.  [CrossRef] [details]
Kundu, N., Chatterjee, P. B., Chaudhury, M. & Tiekink, E. R. T. (2005). Acta Cryst. E61, m1583-m1585.  [CSD] [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Odabasoglu, M., Büyükgüngör, O., Sunil, K. & Narayana, B. (2007). Acta Cryst. E63, o4145-o4146.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626-6635.  [ISI] [CrossRef] [PubMed] [ChemPort]
Xu, Z., Thompson, L. K. & Miller, D. O. (1997). Inorg. Chem. 36, 3985-3995.  [CrossRef] [ChemPort] [ISI]


Acta Cryst (2013). E69, o421  [ doi:10.1107/S1600536813004467 ]

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